Growing a Pre-Seed Startup? This Is The Core Knowledge You Need w/ Ashley Smith

Sep 8, 2025

Ashley Smith, General Partner at Vermilion Cliffs and former marketing leader at Twilio and GitHub, shares invaluable insights for pre-seed founders. She emphasizes the importance of direct customer conversations over investor playbooks. The discussion highlights how successful companies built community engagement to drive growth. Smith advocates for hiring generalists and treating product and marketing as a unified front. Plus, she encourages founders to embrace rejection and craft authentic content in a saturated digital landscape.

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ADVICE

Talk To Customers First

Spend far more time talking to potential customers than chasing investor playbooks or LinkedIn advice.
Ask early users if they'd pay and how much to validate demand before scaling channels.

INSIGHT

Product Equals Marketing Early On

Early-stage product and marketing are the same lever; product is your strongest marketing strategy.
If you lack product-market fit no hiring or sales will sustainably scale growth.

ANECDOTE

How Twilio, Parse And GitLab Grew

Ashley recounts Twilio, Parse and GitLab growth: founders, community, content and relentless shipping powered adoption.
Each company leaned into events, partnerships, content or open development to attract users.

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Pre-seed founders want explosive growth early on, but are you following the wrong playbook too soon? These days strategies, acronyms, and well-intended advice are everywhere, but today's guest argues that the path forward is a simple one: talk to customers, run experiments, and embrace rejection as part of the journey.

In this episode, Yaniv Bernstein speaks to guest Ashley Smith (ex-Twilio, Parse, GitLab, GitHub, and now General Partner at Vermilion Cliffs) and unpacks what it really takes for your startup to go from zero to one. Ashley has been at the helm of some of the most successful developer tool companies in the last decade and now invests in the next generation of technical founders. She shares raw insights from the trenches on how to build community, experiment with growth, and keep your startup alive through grit and iteration.

In this episode, you will:

Learn why investor playbooks can be dangerous for early-stage founders
Understand why customer conversations matter more than LinkedIn hot takes
Discover how product and marketing should be treated as one cohesive strategy
Explore how companies like Twilio, Parse, and GitLab grew by leaning into community, content, and relentless product shipping
See why hiring generalists and “specialists in experimentation” is the best early-stage move
Gain tactical tips on creating authentic founder content in the age of AI slop
Embrace rejection as a natural (and necessary) part of fundraising and early customer acquisition

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